Waltrip played college soccer at the University of South Florida and was a Hermann Trophy candidate in 1999. He was selected in the fifth round of the 2000 MLS Superdraft by the Tampa Bay Mutiny. He opted out of this contract and chose instead to play for Tampere United of the Veikkausliiga in Finland. He spent only one season in Finland then signed with C.D. Olivais e Moscavide of the Portuguese Second Division.
After a short stint in Portugal, Waltrip went back up north to play with Mandalskameratene in Norway. After one successful season there his contract was bought by Sandefjord. In Jaunary 2007, he signed a tree-year contract for Sogndal, but stayed only one season, before signing a two year deal for Molde FK.